I had the same issue. Note 10+ Android Contacts & Calendar Aps wouldn't sync with Outlook Contacts and Calendar Ap. After installing and uninstalling Office 365 Accounts multiple times in the Android settings, which gave me weird error stating that my IT
department had shut off my account, or something like that, I deleted the account in Android settings.
I opened Outlook, tapped on the Office Icon at the top left which opened the menu.
I then tapped the settings icon, then tapped the offending mail account name, and turned on Sync Contacts, and Sync Calendars, which were previously turned off.
I then reset the account, which closed and then reopened the Outlook Ap
I then opened my Android Contacts Ap, and voila, the contacts were there!
I went back to Outlook settings for my offending mail account as per above instructions, and noticed the Calendar Sync button was turned off.
I turned it back on, and when I went to the Android Calendar Ap and it prompted me to Sync the Calendar, which I did, and it synced.
That took care of an initial syncing of calendar and contacts.
I added a contact to Outlook on my PC. It nearly immediately showed up on the phone. However it did not immediately show up in the Android Contacts.
So in the Android Contacts I went to Settings>Manage Contacts>Sync Contacts>Sync.
Eventually it did sync.
I will update my findings as I see how it works over the next few days.